Hydrogen Bromide → HCID 66831615, compound

HRID 2190516Notes

Reaction equation

HRID 2190516 reaction equation
[CH2:1]([N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[BrH:22].[Br:23]Br.C([O-])(O)=O.[Na+]>>[Br:22][C:18]1[C:16]2[C:15](=[N:14][N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:17]=2)[C:21]([Br:23])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 516892Sodium BicarbonateHCID 18949493HCID 18949493, compound

Product 1

HCID 66831615HCID 66831615, compound

Conditions

Temperature
100 °C

Procedure

2-Dodecylbenzotriazole (3.7 g, 13.1 mmol) and an aqueous HBr solution (5.8 M, 15 ml) were added to a flask, and the mixture was stirred for 1 h at 100° C. Bromine (5.9 g, 36 mmol) was added, and the mixture was stirred for 12 h at 135° C. After cooling the mixture to room temperature, an aqueous solution of NaHCO3 was added and the product was extracted with CHCl3. The organic layer was dried over MgSO4 and the solvent was evaporated under reduced pressure. With column chromatography, 4,7-dibromo-2-dodecylbenzotriazole was obtained as light yellow oil (4.3 g, 75%). 1H NMR (400 MHz, CDCl3, δ): 7.36 (s, 2H), 4.60 (t, J=7.0 Hz, 2H), 2.10 (m, 2H), 1.38-1.12 (m, 18H), 0.80 (t, J=6.9 Hz, 3H). 13CNMR (100 MHz, CDCl3, δ): 143.7, 129.4, 109.9, 57.4, 31.8, 30.1, 29.5, 29.5, 29.4, 29.4, 29.3, 28.9, 26.4, 22.6, 14.0.

Workup

  1. stirringthe mixture was stirred for 12 h at 135° C
  2. temperatureAfter cooling the mixture to room temperature
  3. extractionthe product was extracted with CHCl3
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-562750d2182f4ffe8e0f9d668cbdd123
Source dataset
uspto-grants-2012_12
Patent number
US08324400B2

Reaction notes

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